Former Arizona and Mater Dei basketball player Miles Simon, shoots hoops at a park near his Tustin home. He played one season professionally with the Orlando Magic, appearing in five games, before playing in the CBA and overseas.

Mater Dei alum Miles Simon says that his knowledge of the game, not his athleticism, is what made him a better player.

Miles Simon says his only regret about his basketball career is not winning a state title while at Mater Dei. Here he is after a defeat in the state title game to Crenshaw.

Miles Simon led the Arizona Wildcats to the Final Four in 1997 and eventually, won the championship that season. He was named the tournament's Most Outstanding Player.

Tustin resident and Mater Dei alum Miles Simon has enjoyed a successful basketball career in the states and overseas. He is currently a college basketball analyst for ESPN.

While at the University of Arizona, Miles Simon was the NCAA Tournament Most Outstanding Player in 1997. as he led the Wildcats to the NCAA title.

Mater Dei alum and Tustin resident Miles Simon played varsity for four years as a Monarch, winning four CIF titles.

Arizona Wildcats alum Miles Simon, who now lives in Tustin, shoots hoops near his home. He is one of the most decorated college and high school basketball players ever.

Mater Dei alum Miles Simon was the school's first two-time CIF Player of the Year. He helped the Monarchs to four CIF championships.

Mater Dei alum Miles Simon used his high basketball IQ and craftiness to become one of the the most decorated players in Mater Dei basketball history.

Miles Simon was the first two-time CIF Player of the Year for Gary McKnight and the Mater Dei Monarchs.

In an empty, aromatic high school gym, a bunch of grown men play basketball in a local men’s league, watched by a few kids sitting in otherwise empty stands.

No money is involved. The vast majority of the players never touched a court beyond high school. Ages are across the board; more than a few players sport ample midsections.

In this world, Miles Simon still can control a game.

Simon is one of the most accomplished players in Orange County prep history. At Mater Dei, he was the first two-time CIF player of the year. He played college ball at Arizona, leading the team to an NCAA title in 1997. He was an NBA draft pick and played briefly in the league. He made money playing in Italy and Israel.

But, these days, though he looks fit enough by non-NBA standards, Simon describes himself as “not in the best shape.” He’s 38, a middle-of-the-pack age for the men’s league. He makes money coaching basketball and talking basketball and teaching basketball players how to behave. One of the kids in the stands is his.

Playing basketball isn’t his focus.

Still, when Simon does get on the court, all of us take notice. His pedigree is the red cape; his opponents, bulls.

As he dribbles to half court, he’s trapped by two defenders. The ball is taken from his grasp and one of the defenders scores an uncontested layup.

“Get in the weight room, Miles!” shouts the defender.

Simon doesn’t know the man, but responds by citing his own personal life.

“I’ve got three kids, man. That’s the only weight I’m worried about lifting.”

•••

Miles Simon is conflicted. He struggles to even look up as he says words he wishes he could suppress.

“I love Stanley Johnson’s game. As hard as it is for me to say this, he might be the best player to ever come out of Mater Dei.”

Better than you, Miles?

He repeats himself for emphasis. “As hard as it is for me …”

Johnson recently committed to Arizona, Simon’s alma mater, meaning even more of Simon’s legacy is up for the taking at the hands of his successor.

But Simon, a resident of Tustin, isn’t worried. His basketball career has reached heights he didn’t see coming as a teenager. He is in a new phase of life, one shaped by the successes and failures of what has been, in his eyes, an illustrious career.

Still, that career remains a curious case.

From 1991 to ’94, Simon won four CIF titles at Mater Dei. In 1997, Arizona won an NCAA title – becoming the only team to defeat three No. 1 seeds en route to the championship – and Simon was named the tournament’s most outstanding player.

He decided to forgo the NBA draft and return to Arizona for his senior year.

As he explains it, the allure of the NBA, in that day and age, wasn’t enough to pry him away from college.

“I loved college. I loved my experience at Arizona. And mostly, I wanted to win back-to-back titles. We had our whole team coming back. Money was never that important to me. Financially, my family wasn’t struggling.”

Simon entered the NBA draft in the summer of 1998, after the Wildcats lost in the Elite 8. He was selected with the 42nd pick by the Orlando Magic, a team that at the time, boasted the likes of Penny Hardaway, Nick Anderson and Darrell Armstrong. In addition, the 1998-99 season was a strike-shortened season, with teams playing only 50 regular-season games.

“In the shortened season, there wasn’t a lot of time for development. We never practiced, at least that year. And I didn’t get any time. I didn’t get to really learn the position.”

Simon, a 6-foot-3 guard, played five games with the Magic and wasn’t re-signed by the team for the following season, which he sat out with an injured ankle. He then played in the CBA for a few seasons and competed overseas.

“I was kind of a tweener. I played shooting guard my whole life and most people wanted to transition me to point guard. I could pass, but I wasn’t the most skilled ball handler.”

Simon says that in today’s NBA, he would have a better chance to have a long career.

“Back then, the NBA was more about pigeonholing positions. You’re either a point guard or shooting guard. Today, the game is positionless. It’s about just playing the best players.”

In his two years in the CBA, which Simon compares to today’s NBA D-League, Simon became one of the league’s most decorated players. He won league and playoffs MVP, Newcomer of the Year and a championship with the Dakota Wizards in 2002.

“If a guy does that kind of stuff in the D-League today, they’re getting called up for sure,” Simon says. “One hundred percent. But the game has just changed since I stopped playing.”

•••

Simon never catapulted himself back into the NBA.

He played professionally in Italy and Israel after the CBA, but ACL tears in 2003 and 2004 derailed any hopes he had of making it back to the states as a professional.

“That’s when I knew I was done. I was ready to move on to the next phase of my life.”

Today, that next phase is just as fulfilling as Simon could have hoped for as an NBA player.

In 2005, he went back to Arizona to finish his degree and serve as an assistant for Lute Olson, his collegiate coach. He remained until 2008.

Now, he coaches Amateur Athletic Union. basketball and is in his sixth season as an ESPN college basketball analyst. He is also a personal skills trainer for high school, college and professional players.

In short, he’s as involved with the game today as he has been his entire life.

“I still have a competitive desire to win and be in the locker room, so coaching the AAU team and training helps me do that. I get great fulfillment out of helping these young men get better as players. I’ve been involved in basketball since the first grade. I don’t see my involvement ever waning. There is always something new to learn.”

Despite the short tenure of his coaching career, Simon has overseen the AAU careers of several current college players. His latest top recruit is Kentucky freshman Marcus Lee.

“Thinking about my career, it helps me a lot,” he says. “It helps to rely on personal experiences. When I’m coaching, I think back to when I was a player and how I liked to be coached. It helps me know if I’m being too hard on a young man or too easy. Coaching is a lot different because I can’t make a pass or score a basket or defend anybody. But I still get great fulfillment as these young men get better as players.”

Collegiate coaching gigs have crossed Simon’s path since he left Arizona, but he says that the timing wasn’t right.

“Could I see myself coaching again, I could. But could I see myself broadcasting for another 30 years? I absolutely could. It just depends on what’s best for my family.”

•••

Simon was the deer and I was the car.

At least that’s how it played out in my mind.

It’s the championship game of the Costa Mesa High men’s league, Simon’s team against mine. We’re ahead, but Simon and his compatriots, including fellow ESPN analyst Doug Gottlieb, are chopping at our lead.

Simon has a free lane to the basket, where I await for what I’m sure will be an easy block. I mean, he’s old. He can’t really jump anymore. I’m 26, with the wingspan of an albatross and the spring of a new Serta.

The meeting happens. Simon jumps a foot or two off the ground and positions his right shoulder directly into my sternum. Just as I prepare to suggest weightlifting techniques for the veteran baller, I realize I’m not getting any closer to the ball than he wants me to. He finishes with his left hand.

The veteran has outsmarted the young gun.

“I was never the most athletic guy,” Simon says. “Late in high school and through college, I was pretty athletic and was going to dunk on some people but I’ve always been known as a cerebral player. And I pride myself on that.”

He doesn’t remember that single play, but I do. It would be my chance to block the shot of a former Final Four MOP and short-term NBA player.

And Simon is more than happy to be remembered as just that.

“I always wanted to make it to the league. That was my dream as a kid. I made it for a short amount of time, which not very many people do. I was fortunate in that respect.

“Everything else in my life has played out the way it’s supposed to be.”

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